Dierks Bentley‘s trip to Mexico this February will hardly be his first.

In 2005, the Arizona-raised singer married wife Cassidy at a spot south of the border he’d handpicked. But before that, he crossed the border frequently — maybe looking for trouble, maybe not. Bentley, who is one of four headliners for the first-ever Tropical Nights: Boots in the Sand event, Feb. 23-27, held back on some details, but not all.

“We used to go to Tijuana, fairly often,” the star tells Taste of Country. “(There are) a lot of stories I just can’t remember.”

After high school, the ‘I Hold On’ singer spent a year at the University of Vermont before making Nashville his full-time home. Anyone who grew up near a border that protected a younger drinking age knows what he’s talking about. “The second you cross the border, there are people handing you tequila for shots and stuff,” Bentley explains. “It’s pretty wild down there.”

Bentley’s ‘Riser’ album will be in stores on February 25, two days after his performance at the Hard Rock Hotel Maya Riviera. The world-class resort offers a significantly less seedy party than the bars just inside Tijuana, but there’s still plenty of trouble to get into — in a good way.

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